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Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin

Publication ,  Journal Article
El-Feraly, FS; Benigni, DA; McPhail, AT
Published in: Journal of the Chemical Society, Perkin Transactions 1
January 1, 1983

The title compounds were synthesized from their possible biogenetic precursors through hydroperoxide intermediates generated by photo-oxygenation. This route for biological oxygenation may serve as a substitute to epoxidation. The 13C n.m.r. spectral assignments for all intermediates were made. Single-crystal X-ray analyses unequivocally established the 1S configuration in dihydrochrysanolide (14) and its hydroperoxy-analogue (12). lsomorphous crystals of (12) and (14) belong to the monoclinic system, space group P21 with a = 14.350(6), b = 5.882(3), c = 10.343(3) Å, β = 107.64(2)°, Z = 2, for (12), and a = 14.461(6), b = 5.887(3), c = 9.698(4) Å, β = 107.44(2)°, Z = 2, for (14). Least-squares refinement of atomic parameters converged to R 0.040 for (12) and 0.033 for (14) over 1 484 and 1 300 reflections, respectively, measured by diffractometer.

Duke Scholars

Published In

Journal of the Chemical Society, Perkin Transactions 1

DOI

ISSN

1472-7781

Publication Date

January 1, 1983

Start / End Page

355 / 364

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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El-Feraly, F. S., Benigni, D. A., & McPhail, A. T. (1983). Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin. Journal of the Chemical Society, Perkin Transactions 1, 355–364. https://doi.org/10.1039/p19830000355
El-Feraly, F. S., D. A. Benigni, and A. T. McPhail. “Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin.” Journal of the Chemical Society, Perkin Transactions 1, January 1, 1983, 355–64. https://doi.org/10.1039/p19830000355.
El-Feraly FS, Benigni DA, McPhail AT. Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin. Journal of the Chemical Society, Perkin Transactions 1. 1983 Jan 1;355–64.
El-Feraly, F. S., et al. “Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin.” Journal of the Chemical Society, Perkin Transactions 1, Jan. 1983, pp. 355–64. Scopus, doi:10.1039/p19830000355.
El-Feraly FS, Benigni DA, McPhail AT. Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin. Journal of the Chemical Society, Perkin Transactions 1. 1983 Jan 1;355–364.

Published In

Journal of the Chemical Society, Perkin Transactions 1

DOI

ISSN

1472-7781

Publication Date

January 1, 1983

Start / End Page

355 / 364

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry